Asymmetric synthesis of bis-spiro cyclopropane skeletons via bifunctional phosphonium salt-catalyzed [2 + 1] annulation†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-09-23 DOI:10.1039/D4QO01424C

Xiaojun Yu, Fan Wang, Juan Du, Jian-Ping Tan, Jianke Pan, Lixiang Zhu and Tianli Wang

引用次数: 0

Abstract

A new approach for constructing enantiopure spiro[cyclopropane-oxindole] and bispiro[oxindole-cyclopropane-cyclohexone] skeletons featuring three vicinal stereocenters was developed. In this approach, 3-alkenyl-oxindoles and α-bromoketones served as substrates for an asymmetric [2 + 1] cyclopropanation using a chiral bifunctional phosphonium salt catalyst. The reaction afforded the desired products in high yields (up to 97%) and with excellent stereoselectivities (up to 97% ee and >20 : 1 dr).

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通过双功能鏻盐催化的 [2 + 1] 嵌合不对称合成双螺环丙烷骨架

我们开发了一种新方法来构建对映体纯螺环[氯丙烷-吲哚]和双螺[吲哚-环丙烷-环己酮]骨架，其特点是具有三个邻接立体中心。在这种方法中，3-烯基-氧化吲哚和 α-溴酮作为底物，使用手性双官能鏻盐催化剂进行不对称[2 + 1]环丙烷化反应。该反应能以高产率（高达 97%）和优异的立体选择性（高达 97% ee 和 20:1 dr）得到所需的产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.